Categories: C=O Bond Formation > Synthesis of carboxylic acids >
Synthesis of carboxylic acids by hydrolysis or deprotection
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(R)-β-Hydroxy nitriles were obtained via a reduction catalyzed by a
recombinant carbonyl reductase with excellent optical purity and were further
converted to (R)-β-hydroxy carboxylic acids via a nitrilase-catalyzed
hydrolysis. The present study allows ready access to both chiral β-hydroxy
nitriles and β-hydroxy carboxylic acids of pharmaceutical importance.
D. Zhu, H. Ankati, C. Mukherjee, Y. Yang, E. R. Biehl, L. Hua, Org. Lett., 2007,
9, 2561-2563.
Simple, mild, and environmentally friendly procedures for the direct conversion
of dithioesters into either carboxylic acids or esters using hydrogen peroxide
under alkaline conditions are described.
F. Grellepois, C. Portella, Synthesis, 2008,
3443-3446.
The reaction of aldehydes with trichloromethide followed by reductive ring
opening under basic conditions
affords homologated carboxylic acids in high yields. This operationally simple
procedure provides a practical, efficient alternative to other homologation
protocols and is compatible with sensitive aldehydes including enals
and enolizable substrates.
L. R. Cafiero, T. S. Snowden, Org. Lett.,
2008,
10, 3853-3856.
L. R. Cafiero, T. S. Snowden, Org. Lett.,
2008,
10, 3853-3856.
The reaction of alkenyl trichloromethyl carbinols with various nucleophiles
under protic basic conditions reveals that mercaptans participate by
α-substitution (SN2), wheareas hydroxide prefers γ-substitution
with stereoselective allylic transposition (SN2').
Regioselectivity with alkoxides depends upon alkene substitution.
J. L. Shamshina, T. S. Snowden, Org. Lett., 2006, 8, 5881-5884.
The combination of N-hydroxyphthalimide (NHPI), a Co species, and
optionally a small amount of a (per)benzoic acid catalyzes highly efficient
oxidations of alcohols with oxygen. Primary alcohols are rapidly oxidized to the
corresponding carboxylic acids, terminal vic-diols give one carbon less
carboxylic acids, while internal vic-diols were selectively oxidized to
1,2-diketones.
T. Iwahama, Y. Yoshino, T. Keitoku, S. Sakaguchi, Y. Ishii, J. Org. Chem., 2000,
65, 6502-6507.
A one-carbon homologation of an alcohol to the extended carboxylic acid, ester,
or amide involves a Mitsunobu reaction with an alkoxymalononitrile, followed by
unmasking in the presence of a suitable nucleophile. The homologation and
unmasking can even be performed in a one-pot process in high yield.
N. Kagawa, A. E. Nibbs, V. H. Rawal, Org. Lett.,
2016, 18, 2363-2366.